Synthesis of heteroannulated 3-nitro- and 3-aminopyridines by cyclocondensation of electron-rich aminoheterocycles with 3-nitrochromone |
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| Authors: | Viktor O Iaroshenko Satenik Mkrtchyan Ashot Gevorgyan Marcelo Vilches-Herrera Dmitri V Sevenard Alexander Villinger Tariel V Ghochikyan Ashot Saghiyan Vyacheslav Ya Sosnovskikh Peter Langer |
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| Institution: | 1. Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany;2. National Taras Shevchenko University, 62 Volodymyrska st., Kyiv-33 01033, Ukraine;3. Faculty of Chemistry, Yerevan State University, Alex Manoogian 1, 0025 Yerevan, Armenia;4. Hansa Fine Chemicals GmbH, BITZ, Fahrenheitstrasse 1, 28359 Bremen, Germany;5. Department of Chemistry, Ural State University, 51 Lenina Ave., 620083 Ekaterinburg, Russia;6. Leibniz-Institut für Katalyse e. V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock, Germany |
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| Abstract: | 3-Nitrochromone reacts with electron-rich aminoheterocycles (in glacial acetic acid at reflux) and anilines (in a mixture of DMF and TMSCl at 100–140 °C) to give a variety of hetero(carbo)annulated 3-nitropyridines. The reaction, involving a formal 3+3] cyclocondensation, proceeds in high yields and appears not to be influences greatly by the nature of the 1,3-C,N-dinucleophile as seen from the thorough scope study. The synthetic utility of the products was demonstrated by their conversion into the corresponding 3-aminopyridine derivatives. An NMR study and X-ray crystallographic analysis are reported. |
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